US4010214A - Process for the preparation of 2,5-dichloro-p-xylene - Google Patents
Process for the preparation of 2,5-dichloro-p-xylene Download PDFInfo
- Publication number
- US4010214A US4010214A US05/547,067 US54706775A US4010214A US 4010214 A US4010214 A US 4010214A US 54706775 A US54706775 A US 54706775A US 4010214 A US4010214 A US 4010214A
- Authority
- US
- United States
- Prior art keywords
- xylene
- catalyst
- dichloro
- percent
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- UTGSRNVBAFCOEU-UHFFFAOYSA-N 1,4-dichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C=C1Cl UTGSRNVBAFCOEU-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000460 chlorine Substances 0.000 claims abstract description 19
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 19
- 239000003426 co-catalyst Substances 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 11
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 10
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 10
- -1 diaryl sulfides Chemical class 0.000 claims description 6
- MJEPOVIWHVRBIT-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=C(Cl)C=C1 MJEPOVIWHVRBIT-UHFFFAOYSA-N 0.000 claims description 5
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims description 4
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical group C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- LOXRGHGHQYWXJK-UHFFFAOYSA-N 1-octylsulfanyloctane Chemical compound CCCCCCCCSCCCCCCCC LOXRGHGHQYWXJK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910021577 Iron(II) chloride Inorganic materials 0.000 claims description 2
- 229910021576 Iron(III) bromide Inorganic materials 0.000 claims description 2
- RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical compound Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 claims description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 2
- PDWVXNLUDMQFCH-UHFFFAOYSA-N oxoantimony;hydrochloride Chemical compound Cl.[Sb]=O PDWVXNLUDMQFCH-UHFFFAOYSA-N 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 claims description 2
- 101100379081 Emericella variicolor andC gene Proteins 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 10
- 150000004820 halides Chemical class 0.000 abstract description 6
- 229910052742 iron Inorganic materials 0.000 abstract description 5
- 229910052787 antimony Inorganic materials 0.000 abstract description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002898 organic sulfur compounds Chemical class 0.000 abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 239000011593 sulfur Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000005660 chlorination reaction Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UGHIQYNKFXEQPU-UHFFFAOYSA-N 2,3-dichloro-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Cl)=C1Cl UGHIQYNKFXEQPU-UHFFFAOYSA-N 0.000 description 9
- VMMUHZZNIYRBPI-UHFFFAOYSA-N 1,3,4-trichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C(Cl)=C1Cl VMMUHZZNIYRBPI-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- KZNRNQGTVRTDPN-UHFFFAOYSA-N 2-chloro-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Cl)=C1 KZNRNQGTVRTDPN-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- CTSQZGJZQUVGBQ-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3,6-dimethylbenzene Chemical group CC1=C(Cl)C(Cl)=C(C)C(Cl)=C1Cl CTSQZGJZQUVGBQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229910021575 Iron(II) bromide Inorganic materials 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002938 p-xylenes Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
Definitions
- p-xylene can be reacted with chlorine in the presence of a catalyst to produce a mixture of various ring-chlorinated compounds and isomers including 2,5-dichloro-p-xylene, a compound useful as an intermediate in the preparation of pesticides and polymeric materials. Such reactions may be effected in solution, in suspension or in the absence of a solvent.
- p-xylene may be chlorinated in the presence of a catalyst such as iron filings or ferric chloride, to produce mixtures of nuclear chlorinated materials which may then be separated by a series of steps to isolate some components of the mixture.
- p-xylene may be chlorinated, in a solvent, such as carbon tetrachloride, in the presence of a catalyst such as ferric chloride to yield a mixture of mono-, di-, tri-, and tetra- ring-chlorinated p-xylenes which may then be distilled and the dichloro-para-xylene fraction treated with a lower alkanol to recover the commercially desirable 2,5-dichloro-p-xylene.
- a solvent such as carbon tetrachloride
- Divalent sulfur compounds which may be employed as co-catalysts in accordance with the present invention include, for example dialkyl sulfides, diaryl sulfides, alkylaryl sulfides, cyclic sulfides and the like, and mixtures thereof.
- the chlorination process of this invention may be carried out in the presence of a suitable solvent, such as carbon tetrachloride, chloroform, polychloro and perchloroalkanes and the like which is inert to reaction with chlorine under conditions of the chlorination.
- a suitable solvent such as carbon tetrachloride, chloroform, polychloro and perchloroalkanes and the like which is inert to reaction with chlorine under conditions of the chlorination.
- a suitable solvent such as carbon tetrachloride, chloroform, polychloro and perchloroalkanes and the like which is inert to reaction with chlorine under conditions of the chlorination.
- a suitable solvent such as carbon tetrachloride, chloroform, polychloro and perchloroalkanes and the like which is inert to reaction with chlorine under conditions of the chlorination.
- the amount of catalyst system employed may vary considerably, for example from about 0.01 percent by weight or less
- the reaction temperature may vary considerably but is preferably in the range of about 0° to about 100° Celsius, and most preferably in the range of about 25° to about 70° Celsius. It has been found expedient to initiate the reaction at about room temperature, such as 25° Celsius and gradually increase the reaction temperature to about 50° to 70° Celsius during the reaction. Although the process of this invention is preferably carried out at atmospheric pressure, sub-atmospheric or super-atmospheric pressures may be employed, if desired. Upon completion of the reaction, any remaining by-product hydrogen chloride formed during the reaction, and any residual chlorine gas, may be conveniently removed, in a known manner, by blowing air or nitrogen through the mixture.
- the crude chlorination product obtained in accordance with the process of this invention contains, after removal of HCl, about 0 to 6 percent by weight of 2-chloro-p-xylene, about 65 to 80 percent by weight of 2,5-dichloro-p-xylene, about 3 to 20 percent by weight of 2,3-dichloro-p-xylene, about 0 to 8 percent by weight 2,3,5-trichloro-p-xylene and trace amounts, generally less than one percent of 2,3,5,6-tetrachloro-p-xylene.
- This crude product is readily succeptible to simple purification steps to yield a 2,5-dichloro-p-xylene product having a purity in excess of about 90 percent.
- the reaction is run in a solvent may be conveniently removed in a known manner, for example, by distillation. Alternately, the 2,5-dichloro-p-xylene may be obtained directly by filtration of the reaction mixture. If the reaction is run in the absence of a solvent, the solvent separation step is omitted. The crude reaction product may then be treated by crystallization from suitable solvent in which the 2,5-dichloro-p-xylene is substantially insoluble while the major portion of the remaining chlorinated products is soluble.
- Solvents suitable for this purpose include for example, alkanols, especially the lower alkanols such as methanol, ethanol, n-propanol, isopropanol and the various isomeric butanols.
- the preferred solvent for this purpose is isopropanol.
- the amount of alkanol will range from about 0.25 parts to about 10.0 parts by weight and preferably from about 0.5 to about 5.0 parts by weight of solvent per part of crude reaction product.
- the solid portion of the resulting mixture is then filtered, preferably at about room temperature (such as 25° Celsius) and dried.
- the resulting solid will, typically, exhibit a melting point in the range of 64.5° to 66.5° Celsius which corresponds closely to that of 2,5-dichloro-p-xylene of high purity.
- Gas chromatographic analysis of the product thus obtained typically discloses a composition of approximately 94 percent 2,5-dichloro-p-xylene, approximately 4 percent of 2,3-dichloro-p-xylene and approximately 2 percent of 2,3,5-trichloro-p-xylene.
- the product obtained by crystallization from the mixture is 2,5-dichloro-p-xylene having a purity of greater than 90 percent.
- a mixture of about 106 parts of xylene, 0.42 parts of bis (p-chlorophenyl) sulfide and 0.21 parts of antimony trichloride was charged to a reaction vessel at an initial temperature of about 25° C and chlorine was introduced into the reaction mixture.
- the temperature of the reaction mixture was increased gradually to about 67° C during the initial stage of the chlorination reaction and maintained at approximately that temperature during the remainder of the reaction period. Over a total reaction period of approximately four hours a total of about 148 parts of chlorine was introduced into the reaction mixture.
- the reaction mixture was purged with nitrogen to remove hydrogen chloride and any residual chlorine.
- the resulting crude product was analyzed by gas chromatographic methods with the following results:
- Example II The procedure of Example II was repeated except that in place of 0.21 parts of antimony chloride, an equal amount of ferric chloride was employed; maximum reaction temperature was 70° C; and total of 152 parts of chlorine was introduced over a four hour period.
- the crude product was analyzed by gas chromatographic method with the following results:
- a mixture of 106.2 parts of p-xylene, 0.42 parts of bis (p-chlorophenyl) sulfide, 0.21 parts of antimony trichloride, in 100 parts of carbon tetrachloride was charged to a reaction vessel at an initial temperature of about 25° C and chlorine was introduced slowly into the reaction mixture. During the initial stage of the chlorination reaction the temperature was gradually increased to 55° C and maintained at approximately that temperature for the remainder of the reaction period. Over a reaction period of about nine hours, a total of about 159 parts of chlorine was introduced into the reaction mixture.
- the reaction mixture was purged with nitrogen to remove hydrogen chloride and residual chlorine, and solvent removed by distillation.
- the resultant solid was analyzed by gas chromatographic methods with the following results:
- ferric chloride a known prior art catalyst
- ferric chloride a known prior art catalyst
- a mixture of 106.2 parts of p-xylene and 0.53 parts of ferric chloride was charged to a reaction vessel and heated to about 55° C.
- the reaction temperature was maintained at about 55° C to 60° C while 142 parts of chlorine was introduced slowly over a period of about 3 hours.
- the reaction product was purged with nitrogen to remove hydrogen chloride and any residual chlorine.
- the crude product was analyzed by gas chromatographic method with the following results:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/547,067 US4010214A (en) | 1975-02-04 | 1975-02-04 | Process for the preparation of 2,5-dichloro-p-xylene |
| NL7600939A NL7600939A (nl) | 1975-02-04 | 1976-01-30 | Werkwijze voor de bereiding van 2,5-dichloor- -p-xyleen. |
| CA244,980A CA1080751A (en) | 1975-02-04 | 1976-01-30 | Process for the preparation of 2,5-dichloro-p-xylene |
| CH123676A CH622759A5 (enrdf_load_stackoverflow) | 1975-02-04 | 1976-02-02 | |
| BE164035A BE838199A (fr) | 1975-02-04 | 1976-02-02 | Procede pour la preparation de 2,5-dichloro-p-xylene |
| FR7602763*[A FR2300059A1 (fr) | 1975-02-04 | 1976-02-02 | Procede pour la preparation de 2,5-dichloro-p-xylene |
| BR7600645A BR7600645A (pt) | 1975-02-04 | 1976-02-02 | Processo para a preparacao de 2,5-dicloro-p-xileno |
| JP51011213A JPS6026773B2 (ja) | 1975-02-04 | 1976-02-03 | ２．５‐ジクロロ‐ｐ‐キシレンの製造方法 |
| GB4277/76A GB1491841A (en) | 1975-02-04 | 1976-02-03 | Process for the preparation of 2,5-dichloro-p-xylene |
| IT19826/76A IT1054828B (it) | 1975-02-04 | 1976-02-03 | Procedimento per la preparazione di 2.5 dicloro p xilene |
| DE2604277A DE2604277C2 (de) | 1975-02-04 | 1976-02-04 | Verfahren zur Herstellung von 2,5- Dichlor-p-xylol |
| SU762322019A SU627748A3 (ru) | 1975-02-04 | 1976-02-04 | Способ получени 2,5дихлор- -ксилола |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/547,067 US4010214A (en) | 1975-02-04 | 1975-02-04 | Process for the preparation of 2,5-dichloro-p-xylene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4010214A true US4010214A (en) | 1977-03-01 |
Family
ID=24183219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/547,067 Expired - Lifetime US4010214A (en) | 1975-02-04 | 1975-02-04 | Process for the preparation of 2,5-dichloro-p-xylene |
Country Status (12)
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334112A (en) * | 1978-10-05 | 1982-06-08 | Union Carbide Corporation | Process for producing 2,5-dichloro-p-xylene |
| US4520129A (en) * | 1981-08-17 | 1985-05-28 | Phillips Petroleum Compagny | Hydrogenation catalyst |
| US4608448A (en) * | 1978-10-05 | 1986-08-26 | Union Carbide Corporation | Process for producing 2,5-dichloro-p-xylene |
| US4822928A (en) * | 1986-08-05 | 1989-04-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for producing 2,5-dichlorotoluene |
| WO1991013047A1 (en) * | 1990-02-22 | 1991-09-05 | Amoco Corporation | PREPARATION OF 4-BROMO-o-XYLENE |
| US6271426B1 (en) * | 1995-06-13 | 2001-08-07 | Kureha Kagaku Kogyo K.K. | Process for the production of 2,6-dichloro-3,5-di(secondary or tertiary alkyl)toluene |
| KR100421650B1 (ko) * | 1998-06-15 | 2004-03-10 | 키시모토 상교 컴퍼니 리미티드 | 반도체 장치용 절연막 및 반도체 장치 |
| CN101628861A (zh) * | 2009-06-22 | 2010-01-20 | 徐州华日化学工业有限公司 | 一种2,5-二氯对苯二甲醛的合成方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2523104C3 (de) * | 1975-05-24 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2,5-Dichlortoluol |
| DE2702829A1 (de) * | 1977-01-25 | 1978-07-27 | Dynamit Nobel Ag | Verfahren zur herstellung von kernchlorierten xylolen |
| JPS62198068A (ja) * | 1986-02-26 | 1987-09-01 | 日本電気株式会社 | 気密型コネクタ |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1741305A (en) * | 1926-02-04 | 1929-12-31 | Selden Co | Purification of aromatic hydrocarbons |
| US3035103A (en) * | 1959-09-16 | 1962-05-15 | Diamond Alkali Co | Process for preparation and recovery of 2, 5-dichloro-p-xylene |
| US3226447A (en) * | 1960-12-22 | 1965-12-28 | Union Carbide Australia | Directed nuclear substitution-chlorination of aromatic hydrocarbons and halogenated aromatic hydrocarbons |
| US3692850A (en) * | 1970-07-31 | 1972-09-19 | Tenneco Chem | Process for the production of 2,4,5-trichlorotoluene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1022654B (it) * | 1973-10-17 | 1978-04-20 | Hooker Chemicals Plastics Corp | Catalizzatori di orientamento di isomere per la alogenazione di idrocarburi aromatici |
-
1975
- 1975-02-04 US US05/547,067 patent/US4010214A/en not_active Expired - Lifetime
-
1976
- 1976-01-30 NL NL7600939A patent/NL7600939A/xx not_active Application Discontinuation
- 1976-01-30 CA CA244,980A patent/CA1080751A/en not_active Expired
- 1976-02-02 FR FR7602763*[A patent/FR2300059A1/fr active Granted
- 1976-02-02 BE BE164035A patent/BE838199A/xx not_active IP Right Cessation
- 1976-02-02 BR BR7600645A patent/BR7600645A/pt unknown
- 1976-02-02 CH CH123676A patent/CH622759A5/de not_active IP Right Cessation
- 1976-02-03 GB GB4277/76A patent/GB1491841A/en not_active Expired
- 1976-02-03 IT IT19826/76A patent/IT1054828B/it active
- 1976-02-03 JP JP51011213A patent/JPS6026773B2/ja not_active Expired
- 1976-02-04 DE DE2604277A patent/DE2604277C2/de not_active Expired
- 1976-02-04 SU SU762322019A patent/SU627748A3/ru active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1741305A (en) * | 1926-02-04 | 1929-12-31 | Selden Co | Purification of aromatic hydrocarbons |
| US3035103A (en) * | 1959-09-16 | 1962-05-15 | Diamond Alkali Co | Process for preparation and recovery of 2, 5-dichloro-p-xylene |
| US3226447A (en) * | 1960-12-22 | 1965-12-28 | Union Carbide Australia | Directed nuclear substitution-chlorination of aromatic hydrocarbons and halogenated aromatic hydrocarbons |
| US3692850A (en) * | 1970-07-31 | 1972-09-19 | Tenneco Chem | Process for the production of 2,4,5-trichlorotoluene |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334112A (en) * | 1978-10-05 | 1982-06-08 | Union Carbide Corporation | Process for producing 2,5-dichloro-p-xylene |
| US4608448A (en) * | 1978-10-05 | 1986-08-26 | Union Carbide Corporation | Process for producing 2,5-dichloro-p-xylene |
| US4520129A (en) * | 1981-08-17 | 1985-05-28 | Phillips Petroleum Compagny | Hydrogenation catalyst |
| US4822928A (en) * | 1986-08-05 | 1989-04-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for producing 2,5-dichlorotoluene |
| WO1991013047A1 (en) * | 1990-02-22 | 1991-09-05 | Amoco Corporation | PREPARATION OF 4-BROMO-o-XYLENE |
| US6271426B1 (en) * | 1995-06-13 | 2001-08-07 | Kureha Kagaku Kogyo K.K. | Process for the production of 2,6-dichloro-3,5-di(secondary or tertiary alkyl)toluene |
| KR100421650B1 (ko) * | 1998-06-15 | 2004-03-10 | 키시모토 상교 컴퍼니 리미티드 | 반도체 장치용 절연막 및 반도체 장치 |
| CN101628861A (zh) * | 2009-06-22 | 2010-01-20 | 徐州华日化学工业有限公司 | 一种2,5-二氯对苯二甲醛的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2604277C2 (de) | 1984-08-02 |
| GB1491841A (en) | 1977-11-16 |
| IT1054828B (it) | 1981-11-30 |
| BR7600645A (pt) | 1976-08-31 |
| FR2300059B1 (enrdf_load_stackoverflow) | 1979-07-27 |
| NL7600939A (nl) | 1976-08-06 |
| DE2604277A1 (de) | 1976-08-05 |
| JPS51101927A (enrdf_load_stackoverflow) | 1976-09-08 |
| BE838199A (fr) | 1976-08-02 |
| CH622759A5 (enrdf_load_stackoverflow) | 1981-04-30 |
| FR2300059A1 (fr) | 1976-09-03 |
| CA1080751A (en) | 1980-07-01 |
| JPS6026773B2 (ja) | 1985-06-25 |
| SU627748A3 (ru) | 1978-10-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: OCCIDENTAL CHEMICAL CORPORATION Free format text: CHANGE OF NAME;ASSIGNOR:HOOKER CHEMICALS & PLASTICS CORP.;REEL/FRAME:004109/0487 Effective date: 19820330 |